US3325288A - Feed containing inorganic acid salt of 2, 2, 4-trimethyl - 6 - ethoxy - 1, 2-dihydroquinoline - Google Patents
Feed containing inorganic acid salt of 2, 2, 4-trimethyl - 6 - ethoxy - 1, 2-dihydroquinoline Download PDFInfo
- Publication number
- US3325288A US3325288A US474136A US47413665A US3325288A US 3325288 A US3325288 A US 3325288A US 474136 A US474136 A US 474136A US 47413665 A US47413665 A US 47413665A US 3325288 A US3325288 A US 3325288A
- Authority
- US
- United States
- Prior art keywords
- dihydroquinoline
- trimethyl
- ethoxy
- acid salt
- carotene
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L3/00—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs
- A23L3/34—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals
- A23L3/3454—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals in the form of liquids or solids
- A23L3/3463—Organic compounds; Microorganisms; Enzymes
- A23L3/3544—Organic compounds containing hetero rings
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K30/00—Processes specially adapted for preservation of materials in order to produce animal feeding-stuffs
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/04—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms
- C07D215/06—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms having only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
Definitions
- This invention relates to new and improved antioxidants useful in animal foods for preventing the loss of vitamins A and E, and other components known to deteriorate through oxidation. More specifically, the invention is directed to the preparation of certain salt derivatives of dihydroquinolines which are more effective antioxidants than are the free dihydroquinoline bases.
- dihydroquinolines of the following formula are herein referred to as free bases and are known to have antoxidant properties:
- alkyl and alkoxy substituents include, for example, methyl, ethyl, n-propyl, isopropyl, nbutyl, isobutyl, tertiary 'butyl, amyl, methoxy, ethoxy, n propoxy, isopropoxy, n-butoxy, isobutoxy, tertiary butoxy, amyloxy and the like.
- improved antioxidants can be prepared by reacting the dihydroquinolines with strong inorganic acids, such as sulfuric, phosphoric, hydrochloric, hydrobromic and sulfurous acid.
- improved antioxidants prepared by reacting the 2,2,4-trimethyldihydroquinolines with these acids in addition to being superior antioxidants are free-flowing solid products which are readily adaptable to formulation with fibrous or amorphous substances.
- the new compounds are salts of the dihydroquinolines and are prepared by dissolving the dihydroquinoline in a suitable solvent in which the salts are insoluble.
- suitable solvents include the hydrocarbons such as benzene, toluene, xylene, petroleum ether, gasoline, kerosene and other petroleum fractions, the ketones, such as acetone and methyl ethyl ketone; and the ethers, such as diethyl ether.
- elevated temperatures within the range of a from about 30 C. to the reflux temperatures of the reaction mixtures are required to effect a complete reaction and formation of the desired salt.
- Example 2 A reaction flask was charged with 108.5 grams of 2,2,4-trimethyl-6-ethoxy-1,Z-dihydroquinoline and 150 ml.
- Example 3 A reaction flask was charged with 43.4 grams of 2,2,4-trimethyl-6-ethoxy4,Z-dihydroquinoline and 50 ml. of acetone. The flask and its contents were heated to reflux temperature and 32.2 grams of phosphoric acid (H PO were added. During one hour acetone and water were evaporated. Anhydrous acetone in the amount of 50 ml. was added to the reaction mixture and upon standing at room temperature a White crystalline salt, M.P.
- H PO phosphoric acid
- the following table sets forth the percentage of the original carotene remaining after the two weeks treatment. Six replicates of each of the treated alfalfa samples were analyzed before and after the heat treatment. The treated samples of alfalfa included some with 0.015 percent by weight of the free base 2,2,4-trimethyl-6-ethoxy-1,Z-dihydroquinoline or the salt.
- Example 2 carotene content, the content after two weeks at 55 C. and the percentage retained.
- Example 3 The stabilizing effects of 2,2,4-trimethyl-6-ethoxy-1,2- dihydroquinoline and salts thereof were studied on carotene in mixtures of corn oil and alfalfa stored in cotton bags at room temperatures (23 C. to 26 C.) for two months. The following observations were made.
- balanced feeds may contain Whole grains or process grains, animal and vegetable oils, minerals, antibiotics, steroids, anthelmintics, supplemental vitamins and other compounds which are conventional in the animal feed industries.
- Such conventional feeds may be benefited by the incorporation of from 0.001 to 0.20 percent by weight of the described salts of the substituted 2,2,4-trimethyl-1,2-dihydroquinoline; preferred practice may utilize from 0.005 to 0.05 percent by weight of the said salts.
- An animal feed comprising a feed component containing a compound selected from the group consisting of carotene and vitamin A, said animal feed containing from about 0.001 to about 0.20 percent by weight of an inorganic acid salt of 2,2,4-trimethyl-6-ethoxy-1,2-dihydroquinoline.
- An animal feed comprising a feed component containing a compound selected from the group consisting of carotene and vitamin A, said animal feed containing from about 0.001 to about 0.20 percent by Weight of the hydrochloric acid salt of 2,2,4-trimethyl-6-ethoxy-1,2-dihydroquinoline.
- An animal feed comprising a feed component containing a compound selected from the group consisting of carotene and vitamin A, said animal feed containing from about 0.001 to about 0.20 percent by weight of sulfuric acid salt of 2,2,4-trimethyl-6-ethoxy-1,2-dihydroquinoline.
- An animal feed comprising a feed component containing a compound selected from the group consisting of carotene and vitamin A, said animal feed containing from about 0.001 to about 0.20 percent by weight of a phosphoric acid salt of 2,2,4-trimethyl-6-ethoxy-1,2-dihydroquinoline.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nutrition Science (AREA)
- Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Microbiology (AREA)
- Animal Husbandry (AREA)
- Zoology (AREA)
- Fodder In General (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19641492900 DE1492900A1 (xx) | 1963-08-07 | 1964-07-27 | |
BE651405D BE651405A (xx) | 1963-08-07 | 1964-08-05 | |
NL6408961A NL6408961A (xx) | 1963-08-07 | 1964-08-05 | |
FR984398A FR1404848A (fr) | 1963-08-07 | 1964-08-06 | Procédé de préparation d'antioxydants utiles dans les aliments pour animaux et nouvelles compositions alimentaires ainsi obtenues |
GB32066/64A GB1074236A (en) | 1963-08-07 | 1964-08-06 | Animal feed compositions comprising dihydroquinoline salts |
LU46716D LU46716A1 (xx) | 1963-08-07 | 1964-08-07 | |
US474136A US3325288A (en) | 1963-08-07 | 1965-07-22 | Feed containing inorganic acid salt of 2, 2, 4-trimethyl - 6 - ethoxy - 1, 2-dihydroquinoline |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US30062363A | 1963-08-07 | 1963-08-07 | |
US33373063A | 1963-12-26 | 1963-12-26 | |
US34392664A | 1964-02-11 | 1964-02-11 | |
US474136A US3325288A (en) | 1963-08-07 | 1965-07-22 | Feed containing inorganic acid salt of 2, 2, 4-trimethyl - 6 - ethoxy - 1, 2-dihydroquinoline |
Publications (1)
Publication Number | Publication Date |
---|---|
US3325288A true US3325288A (en) | 1967-06-13 |
Family
ID=27501777
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US474136A Expired - Lifetime US3325288A (en) | 1963-08-07 | 1965-07-22 | Feed containing inorganic acid salt of 2, 2, 4-trimethyl - 6 - ethoxy - 1, 2-dihydroquinoline |
Country Status (6)
Country | Link |
---|---|
US (1) | US3325288A (xx) |
BE (1) | BE651405A (xx) |
DE (1) | DE1492900A1 (xx) |
GB (1) | GB1074236A (xx) |
LU (1) | LU46716A1 (xx) |
NL (1) | NL6408961A (xx) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3883673A (en) * | 1969-07-22 | 1975-05-13 | Solomon Aronovich Giller | Stabilization of carotene |
US4363910A (en) * | 1979-02-21 | 1982-12-14 | Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara R.T. | 2,2-Dimethyl-1,2-dihydroquinoline derivatives useful as antioxidants |
US4490394A (en) * | 1979-02-21 | 1984-12-25 | Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara R.T. | 2,2-Dimethyl-1,2-dihydroquinoline derivatives useful as antioxidants, a process for the preparation thereof and mixtures containing them |
WO1989005994A1 (en) * | 1987-12-23 | 1989-06-29 | Traqson Limited | Photochemical marking of substrates |
US4986996A (en) * | 1988-07-08 | 1991-01-22 | University Of St. Andrews | Ethoxyquin derivatives as antioxidants in edible oils and fish meal |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2562970A (en) * | 1950-04-14 | 1951-08-07 | Thompson Chester Ray | Preservation of forage crops |
US2897119A (en) * | 1957-11-12 | 1959-07-28 | Camp Sea Food Company Inc Van | Stable powdered oil soluble vitamins and method of preparing stable powdered oil soluble vitamins |
US2935449A (en) * | 1958-04-14 | 1960-05-03 | Pfizer & Co C | Stabilized vitamin a compositions |
-
1964
- 1964-07-27 DE DE19641492900 patent/DE1492900A1/de active Pending
- 1964-08-05 NL NL6408961A patent/NL6408961A/xx unknown
- 1964-08-05 BE BE651405D patent/BE651405A/xx unknown
- 1964-08-06 GB GB32066/64A patent/GB1074236A/en not_active Expired
- 1964-08-07 LU LU46716D patent/LU46716A1/xx unknown
-
1965
- 1965-07-22 US US474136A patent/US3325288A/en not_active Expired - Lifetime
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2562970A (en) * | 1950-04-14 | 1951-08-07 | Thompson Chester Ray | Preservation of forage crops |
US2897119A (en) * | 1957-11-12 | 1959-07-28 | Camp Sea Food Company Inc Van | Stable powdered oil soluble vitamins and method of preparing stable powdered oil soluble vitamins |
US2935449A (en) * | 1958-04-14 | 1960-05-03 | Pfizer & Co C | Stabilized vitamin a compositions |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3883673A (en) * | 1969-07-22 | 1975-05-13 | Solomon Aronovich Giller | Stabilization of carotene |
US4363910A (en) * | 1979-02-21 | 1982-12-14 | Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara R.T. | 2,2-Dimethyl-1,2-dihydroquinoline derivatives useful as antioxidants |
US4490394A (en) * | 1979-02-21 | 1984-12-25 | Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara R.T. | 2,2-Dimethyl-1,2-dihydroquinoline derivatives useful as antioxidants, a process for the preparation thereof and mixtures containing them |
WO1989005994A1 (en) * | 1987-12-23 | 1989-06-29 | Traqson Limited | Photochemical marking of substrates |
US4986996A (en) * | 1988-07-08 | 1991-01-22 | University Of St. Andrews | Ethoxyquin derivatives as antioxidants in edible oils and fish meal |
Also Published As
Publication number | Publication date |
---|---|
NL6408961A (xx) | 1965-02-08 |
LU46716A1 (xx) | 1964-10-07 |
BE651405A (xx) | 1964-12-01 |
DE1492900A1 (xx) | 1970-08-27 |
GB1074236A (en) | 1967-07-05 |
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